17 Proven Tactics to Grow and Monetize Your Online Business

Today we’re sharing proven ways to grow your email list, engage your target audience, and ultimately make more money in your business.

Chenell Basilio is back on the Side Hustle Show. She’s the longtime listener turned go-to source for online business growth case studies, and she runs GrowthInReverse.com along with the Growth in Reverse podcast.

A common theme in this episode is tapping into other people’s audiences, often on social media, in a way that’s tasteful and tactful instead of spammy.

Chenell brought 17 real examples from other newsletter owners and creators, grouped into three buckets: growing your list, keeping subscribers engaged, and turning subscribers into paying customers.

Tune in to Episode 747 of the Side Hustle Show to learn:

creative, low-cost ways to grow your email list
how to keep subscribers opening and clicking your emails
tactics that turned small lists into real revenue

Table of Contents show

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Growing Your Email List (GROWTH)

These six tactics show how real newsletter owners picked up new subscribers, from one well-placed Reddit comment to a 30-day challenge.

1. Using Reddit to Get to 5,800 Subscribers (Michelle Rueda)

Michelle Rueda runs What’s Weird ATX, an Austin events newsletter, and grew it to 5,800 subscribers with zero ad spend.

Her process:

Lurk in a subreddit first to learn what people respond to
Build up karma by replying genuinely before ever mentioning her newsletter.
When she does answer a question, she gives a full, useful answer first, then mentions she shares similar tips weekly in her newsletter and drops the link.

One comment on a “things to do in Austin that don’t involve drinking” thread alone brought in 1,500 new subscribers in just a few days. Chenell says this approach can be repeated in any local subreddit.

2. The 30,000-Subscriber Giveaway (Aleyda Solis)

Aleyda Solis runs SEO FOMO, a newsletter for SEO professionals. Instead of a standard giveaway, she framed it as a shared goal: help me hit 30,000 subscribers.

She partnered with SEO software companies to give away tools her readers already wanted, like free six months to a year of access, rather than generic prizes.

People entered by subscribing, then earned extra entries by referring other SEO pros. The giveaway ran from October 1 to November 19, about seven weeks, until she hit the number.

Tools like SparkLoop or Viral Loops can track referral entries like this.

3. The “2-Step” LinkedIn Post (Daniel Bustamante)

Daniel Bustamante of Premium Ghostwriting Academy updated the classic “comment a keyword to get my free resource” LinkedIn post, which has lost steam as more people catch on.

His version delivers real value in the post itself, then offers a deeper resource through a comment-triggered reply.

Because the post already stands on its own, commenters are people genuinely interested in the topic, not just freebie hunters. Posts like this regularly bring in 1,300 to 2,000 comments for Daniel.

4. A 12-Day Holiday Giveaway (Fab Giovanetti)

Fab Giovanetti ran a “12 Days of Christmas” giveaway, partnering with 12 different tools and communities to give away a new prize each day.

She sent a new offer to her list daily and promoted it on LinkedIn, asking readers to share it. The campaign added about 550 new subscribers.

Because every prize was something her specific audience actually wanted, the new subscribers stuck around, and click-through rates and open rates went up afterward too.

5. A One-Word Button Change (Max Bidna, Marketing Max)

Max Bidna, who runs the newsletter Marketing Max, tested changing his subscribe button from “Subscribe” to “Continue”. That single word swap boosted his landing page conversion rate 5x, same offer, same traffic. Marketing Max now has 182,000 newsletter subscribers.

Chenell notes results vary by site, so it’s worth testing your own page; she’s used tools like Crazy Egg and Leadpages to run similar tests.

6. A 30-Day Challenge as a Lead Magnet (Jess Campbell)

Jess Campbell, of Out in the Boons, helps nonprofits make money through email marketing.

Inspired by Chenell’s own 30 Days of Growth format, she wrote her own 30-day challenge herself, one actionable tip a day, instead of crowdsourcing tips from other creators.

She promoted it with six or seven LinkedIn posts and her email list. The challenge brought in 440 new subscribers, and a few became paying clients.

Keeping Subscribers Engaged (ENGAGEMENT)

Once someone joins your list, the real work starts. Here’s how six creators kept subscribers opening, clicking, and sticking around.

7. Cutting a Signup Step Reduced Churn by 57% (Half Baked)

Half Baked, a daily startup ideas newsletter at gethalfbaked.com with 125,000+ subscribers, used to ask new subscribers several questions right after signup, before a thank-you page.

That extra friction was driving people away within their first 30 days, especially subscribers coming from paid Meta ads who didn’t know the brand yet.

The team cut it down to just name and email, sending people straight to a welcome page and asking extra questions later. That single change cut 30-day churn by 57%.

8. A Pre-Event Video That Got 99% to Show Up (Sam Vander Wielen)

Sam Vander Wielen, an attorney who helps online entrepreneurs, had 11,000 people sign up for a webinar. She sent each one a personal welcome video using a tool called Video Ask, asking what they wanted her to cover.

Everyone who replied got a custom video response back, over 300 in total. Among the people she personally responded to, show-up rates hit close to 99%, and more than half of attendees bought her $2,000+ product. She now uses the same approach for her podcast and newsletter, not just webinars.

9. Mining Your Own Email Data With AI (Dan Cumberland)

Dan Cumberland exported six months of his own email broadcast data and asked an AI tool to find patterns behind his best-performing subject lines.

He expected the answer to involve numbers or bold claims, but instead the AI surfaced five structural patterns, things like a contrarian claim, an unexpected comparison, or a first-person confession, that separated his best subject lines from his worst.

Chenell says anyone can try this with their own email platform’s export to find what actually works for their specific list, instead of following generic best practices.

10. A 4-Email Sequence to Win Back Inactive Subscribers (Joanna, The Assist)

Joanna runs The Assist, a professional development newsletter with 300,000 subscribers sent three to four times a week.

Instead of one generic “are you still there?” email, she built a 4-email reactivation sequence for subscribers who hadn’t opened anything in 30 days: email one helps people whitelist the newsletter in case it’s landing in spam, email two reintroduces the brand, email three is the direct ask, and email four is the final notice before unsubscribing.

11. A 4-Hour Follow-Up Email That Boosted Engagement (Jason Resnick)

Jason Resnick, of NurtureKit, sends a second email exactly 4 hours after delivering a lead magnet, but only to subscribers who haven’t opened or clicked the first one.

The follow-up is short and casual: did you get the free thing, and what are you hoping to learn?

He personally replies to responses, which often leads to real conversations and consulting inquiries. His engaged subscriber rate jumped from 48% to 67% after adding this one email.

12. A “Take a Break” Link Instead of Unsubscribe (Chenell Basilio)

Chenell borrowed this idea from a newsletter called Two Sigma: instead of just an unsubscribe link, the footer offers a “snooze” option that pauses emails for 30 days for subscribers feeling overwhelmed.

Because simple link-click triggers aren’t reliable for everyone (some corporate firewalls click every link automatically), Chenell built her own version with a Tally form that captures the subscriber’s email through Kit and auto-tags them to pause.

The tweak has saved over 400 subscribers who might otherwise have unsubscribed for good.

Turning Your List Into Revenue (MONETIZATION)

Growing a list is only half the job. Here’s how five creators turned subscribers into real revenue.

13. A 7-Figure List With Under 4,000 Subscribers (Dustin Riechmann)

Dustin Riechmann, who previously grew Fire Creek Snacks using podcast guesting, now runs Seven Figure Leap, a podcast guesting academy.

His list brings in about $285 per subscriber per year, far above the rough industry benchmark of roughly $12 per subscriber per year.

His strategy: instead of pitching shows directly in his niche, he guests on “shoulder” podcasts, shows whose audience overlaps with his ideal customer without being a direct competitor, like a parenting or personal finance show.

He demonstrates expertise live while guesting, then funnels listeners into his program.

14. One Welcome Email Question That Doubled Sales (Katelyn Bourgoin)

Katelyn Bourgoin, of Why We Buy, asks new subscribers a single question in her welcome email: what do you need help with most right now?

Their answer, tracked with Kit polls, sorts them into a group that later receives a flash sale for the matching product instead of a generic offer. If they don’t buy, they get a flash sale for a different product a few months later. The approach also works with affiliate offers, not just your own products.

Her digital product sales rose 30% in the first three months and have doubled over time.

15. Pitching Sooner Tripled Sales (Matt Ragland)

Matt Ragland, of Good People Digital, flipped the usual welcome sequence script.

Instead of waiting months to make an offer, he pitches a low-ticket product, around $9 to $29, within the first seven days, while new subscribers are still excited to be on the list.

Buyers move on to bigger offers later; non-buyers get a gentle repitch a few weeks on. The goal is building a list of buyers rather than freebie collectors, since people who won’t buy a $9 product are unlikely to buy a $1,000 one either.

This approach has tripled sales compared to waiting to pitch.

16. A Self-Monetizing Lead Magnet (Terry Rice)

Terry Rice kept getting asked the same question: how does he run two businesses, speak professionally, and raise four kids without burning out?

Instead of answering one email at a time, he built a free interactive tool with Lovable, no code required, that shows his real daily dashboard. Every resource linked inside it is an affiliate link, so the tool earns money whether or not someone buys his core product.

It’s also brought in coaching clients who want to learn how he does it all. Subscriber growth jumped from less than one new subscriber a day to about 50 a week.

17. The FOMO Approach to Sponsors (Bay Area Times)

The Bay Area Times, a Silicon Valley business and tech newsletter, has an “advertise with us” link in every issue’s footer.

Clicking it signs potential sponsors up for a separate email list with its own welcome email, sent from a different address, that functions like a media kit.

From there, sponsors get periodic updates with fresh growth numbers, like a recent one announcing 215,000 subscribers, and examples of past sponsorships. By the time a sponsor is ready to buy, they already feel like they know the newsletter, which means faster decisions and less price negotiation.

What’s Next for Chenell?

Chenell’s main focus right now is writing more deep dives and getting nerdier about reverse engineering how newsletters grow, basically doing more of what she already does best at Growth in Reverse.

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